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Bennett's parents, Leilani (née Dorsey Bennett) and Ronald Keeling,[3][4] met in church and hitchhiked to Florida while Leilani was pregnant with her.[5] She is of English, Scottish, Irish, German and Lithuanian descent. She was born in Fort Myers, Florida and raised in Naples, Florida.[3] Her parents divorced when Bennett was six and she moved to Ohio with her father, who opened an automobile repair shop.[5] They moved regularly around the state, with Bennett saying: "there was no time when I lived anywhere longer than two years. I was always a social outcast. Maybe I didn't care what people thought because I [thought], 'Well, I probably won't stick around here for too long'."[5]

Bennett describes her childhood as "nomadic", as she moved between living with her father in Ohio and her mother in Florida: "I lived somewhat of a nomadic life even when I lived in Ohio. We spent time in rural areas, in suburban areas, never really city areas. We rode four-wheelers. We had pigs and ferrets. And creeks. We had a creek in my backyard. It was like Huckleberry Finn... I was kind of a tomboy for awhile. It's tough to explain because I grew up with my mom and my dad simultaneously but separately because they weren't together. So I kind of get femininity from my mother and boyishness from my dad. He loved fishing, he loves hunting, he loves boating, and football, baseball, and basketball. So that really saturated my life. And then my mother was very soft and also strong, but more of an artist. So I kind of had the best of both worlds."[6]

When Bennett was 10, she and her father moved to Stow, Ohio, where she attended Stow-Munroe Falls High School and at 13, she enrolled at Barbizon Modeling School of Akron, Ohio.[4] She attended the International Modeling and Talent Convention in 2001 and 2006, where she won a major award,[4] acted in school plays and sang in choirs.[2] She also lived with her mother in Naples occasionally, where she attended Barron G. Collier High School, where she studied music and acting.[7] When Bennett was 18, she persuaded her mother to take her to Los Angeles for three months to pursue an acting career. Just as she was about to return home, she managed to secure representation by claiming to her prospective agent that a highly-regarded agency had approached her. The agent refused to lose Bennett and signed her.[5] Bennett began using her mother's maiden name as her stage name.[2][8]

In what was only her third audition,[5] Bennett won the role of popstar Cora Corman for her film debut in the 2007 romantic comedy Music and Lyrics, with Hugh Grant and Drew Barrymore.[9] Bennett sang several songs for the film's soundtrack, including "Buddha's Delight" and "Way Back into Love"; fragments of the songs "Entering Bootytown" and "Slam" are heard during concert scenes in the film, and her song "Invincible" plays during the end credits. That same year, she signed with 550 Music/NuSound Records (part Epic Records), and began working on her debut album, though one was never released. Bennett performed her first live concert at The Mint in Los Angeles on June 19, 2008.

Despite the auspicious debut, Bennett did not break through. She said in an interview in June 2016: "It’s been kind of a long journey for me. Everyone has a different path; I guess you hear them all. I don’t know how common mine is. I didn’t have a long-term plan or goal. All I came to Los Angeles with was a dream. No one from my family ever left Ohio. In L.A., I saw a lot of talent wasted because of fear. The odds are really stacked against you. I was a bit like Dorothy following the yellow brick road I guess. Except there was no good witch... Nothing came that easily ever again [after Music and Lyrics]. It was a good start—I’m grateful for the experience, but I wanted more. After that film, I ventured back out into the darkness, as actors often do. And I was completely engulfed by it. I got lost, I got broke. I got heartbroken by the roles I’d never have a chance to play, because you know how it is. Even when a filmmaker pointed at me and said, "I want to put you in this film," it never happened because of the financial aspect of our industry. I wasn’t a bankable name, I guess. But it went on like this, on repeat, for many years. I begged, I struggled, I fought. There was no other option, really.[10]